Dukes County MA Homes for Sale

/4
$3,495,000
- Land
- 28,314 Sq Ft
- $5,376,923 per Acre
48 Plaintingfield Way Unit 10, Edgartown, MA 02539

Set on an exceptional .65 -acre parcel, this rare offering combines privacy, space, and an unbeatable location just moments from town and the water. The expansive lot offers a unique opportunity to expand and create a custom estate tailored to your vision. Surrounded by mature landscaping and generous outdoor space, the property offers a peaceful retreat while remaining conveniently close to

Julia Smith Donnelly + Co

48 Plaintingfield Way Unit 10, Edgartown, MA 02539
/32
$1,595,000
- 3 Beds
- 3.5 Baths
- 2,739 Sq Ft
40 Hidden Cove Rd Unit 2, Oak Bluffs, MA 02557

Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a

Rose Ryley Wallace & Co. Sotheby's International Realty

40 Hidden Cove Rd Unit 2, Oak Bluffs, MA 02557
/19
$799,000
- Land
- 2.1 Acres
- $380,476 per Acre
42 Field View Ln Unit 79, West Tisbury, MA 02575

Nestled among the open fields of West Tisbury, this beautiful building parcel offers apeaceful, bucolic setting with endless potential. An eclectic artists' camp graces theproperty, creating a unique sense of character and inspiration. Meandering walking trailswind through a diverse landscape of pine, oak, and beech trees, inviting you to exploreand enjoy the natural surroundings.

kyle Neyer Tea Lane Associates

42 Field View Ln Unit 79, West Tisbury, MA 02575
/31
$1,700,000

$150K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,784 Sq Ft
12 Lobsterville Rd, Aquinnah, MA 02535

Aquinnah is a remote, culturally rich town on the western tip of Martha's Vineyard. Formerly known as Gay Head is world-renowed for its dramatic, multicolored clay cliffs and is the historic homeland of the Wampanoag Tribe.Frank Nuovo fell in love with this piece of land and decided to build this house in 1986. He was an avid hunter and fisherman. In 1996 he won 1st place in the famous

Carol McManus C McManus Realty Group

12 Lobsterville Rd, Aquinnah, MA 02535
/28
$1,595,000
- 3 Beds
- 3.5 Baths
- 2,739 Sq Ft
40 Hidden Cove Road Unit 2 Unit 2, Oak Bluffs, MA 02557

Enjoy timeless summers at this Hidden Cove condo, where days begin with a paddle on Sengekontacket Pond, afternoons are spent between the pool and tennis courts, and evenings end on the deck after a day spent exploring the island. This three-bedroom unit has distant water views and offers an easy, multi-level floor plan with open living spaces, a private primary suite, two guest bedrooms, a

Rose Ryley Wallace & Co. Sotheby's International Realty

40 Hidden Cove Road Unit 2 Unit 2, Oak Bluffs, MA 02557
/6
$3,750,000
- Land
- 3.6 Acres
- $1,041,667 per Acre
131 Pond View Farm Rd Unit 1-7, West Tisbury, MA 02575

Set on a picturesque peninsula along Tisbury Great Pond, this exceptional pondfront parcel offers a rare opportunity to own a piece of Martha's Vineyard's rural landscape. Currently used for equestrian activities, the expansive open acreage is nestled in one of the Island's most beautiful and unspoiled settings, evoking West Tisbury's rich agricultural heritage. This property is a blank slate,

Meg Bodnar Tea Lane Associates

131 Pond View Farm Rd Unit 1-7, West Tisbury, MA 02575
/39
$3,495,000
- 4 Beds
- 4 Baths
- 3,200 Sq Ft
64 Christiantown Rd, Vineyard Haven, MA 02568

This stunning 3,200 sq. ft. architectural home features a bright, open layout defined by vaulted ceilings and rich hardwood floors. The gourmet kitchen, appointed with high-end finishes including silestone countertops, flows seamlessly into both a cozy family room and an elegant living room, anchored by a gorgeous dual-sided brick fireplace. With 4 bedrooms, 4 full bathrooms, and 2 dedicated home

Karen Overtoom Karen M. Overtoom R.E.

64 Christiantown Rd, Vineyard Haven, MA 02568
/10
$896,000
- 2 Beds
- 1 Bath
- 834 Sq Ft
21 Clay Pit Rd, Edgartown, MA 02539

This home is walk in ready to enjoy while you let your imagination go to work for this ideal property. Located a short walk along the bike path to Post Office square you will find this quiet location is perfect. You feel the old Vineyard charm along this peaceful lane. This represents the best entry way into Edgartown Real Estate today so do not let this opportunity pass you by. A 3rd bedroom

Jim Joyce Carroll & Vincent R.E.

21 Clay Pit Rd, Edgartown, MA 02539
/20
$1,745,000
- 2 Beds
- 1 Bath
- 560 Sq Ft
11 Beach Rd, Oak Bluffs, MA 02568

Oceanfront Cottage on .21 acre of waterfront property and over 50ft of shoreline on East Chop. Wake up to breathtaking ocean views and the soothing sound of waves from this charming two-bedroom oceanfront cottage. Perfectly positioned along the shoreline, this inviting coastal retreat offers the rare opportunity to own a slice of waterfront paradise. Designed for relaxed seaside living, the home

Carleen Cordwell Anchor Realty of Martha's Vineyard

11 Beach Rd, Oak Bluffs, MA 02568
/29
$1,550,000
- 4 Beds
- 2 Baths
- 1,757 Sq Ft
8 Rumpus Ridge Rd, Chilmark, MA 02535

Escape to your own getaway with mature landscaped gardens and privacy in the heart of Chilmark. Walk to the Chilmark Store, library, Chilmark Community Center, Beetlebung Farm and bank. Access to Chilmark beaches - Lucy Vincent and Squibnocket - and Menemsha Public Beach are a plus.This four bedroom, two bath home has hardwood floors throughout. The living room and eat-in kitchen separate the

Julianna Flanders Flanders Real Estate

8 Rumpus Ridge Rd, Chilmark, MA 02535
/7
$349,000
- Land
- 1.26 Acres
- $276,984 per Acre
00 Moshup Trail Unit 27 & 146, Aquinnah, MA 02535

Lovely beach lot off Moshup Trail in Aquinnah. Enjoy the sandy beach, Atlantic Ocean water and beauty of the South shore. This private beach lot is shared with only seven other members. Parking is located a short walk across the road from the beach access.Private parking limited to one car per member. This is not a buildable lot.

Julianna Flanders Flanders Real Estate

00 Moshup Trail Unit 27 & 146, Aquinnah, MA 02535
/30
$2,295,000
- 5 Beds
- 4 Baths
- 3,119 Sq Ft
2 Old Pocha Rd, Edgartown, MA 02539

Tucked away down a quiet country road, this one-of-a-kind Chappaquiddick retreat invites you to exhale the moment you arrive. With no visible neighbors and the sounds of nature all around, the property offers a rare sense of privacy, peace, and timeless island charm. Built in an era when homes were crafted with artistry and intention, this distinctive post-and-beam residence blends warmth,

Jim Feiner Feiner Real Estate

2 Old Pocha Rd, Edgartown, MA 02539
/7
$1,150,000
- Land
- 1.09 Acres
- $1,055,046 per Acre
30 Double Ox Rd Unit 33, Oak Bluffs, MA 02557

Create an extraordinary Martha's Vineyard estate in the exclusive Lagoon Ridge community of Oak Bluffs. This mostly wooded estate parcel of over one acre features gently rolling topography, providing an exceptional canvas for a custom-designed luxury residence. Privately situated within an intimate enclave of just four estate parcels, the property is accessed by a welcoming paved approach. This

Marilyn Moses Ocean Park Realty Inc

30 Double Ox Rd Unit 33, Oak Bluffs, MA 02557
/20
$1,149,000
- 3 Beds
- 2 Baths
- 1,373 Sq Ft
72 Moonstone Way, Vineyard Haven, MA 02568

Nestled in a quiet neighborhood just a short stroll from Lake Tashmoo and less than a mile from Main Street, Owen Park Beach, and the Steamship Authority, this lovingly maintained Colonial Saltbox offers the perfect blend of comfort, convenience, and island charm. With a strong rental history, the home is ideally suited as a vacation getaway, year-round residence, or investment property. The

Carol Shore Donnelly + Co

72 Moonstone Way, Vineyard Haven, MA 02568
/34
$2,195,000
- 3 Beds
- 3 Baths
- 2,363 Sq Ft
139 Tea Ln, Chilmark, MA 02535

Tucked away on a quiet country road in a serene Chilmark setting, this beautifully crafted home, built in 2023, offers modern comfort surrounded by natural beauty. The thoughtfully designed main level features an open, light-filled floor plan where the living, dining, kitchen, and family areas flow seamlessly together. A wall of glass doors opens to the outdoors, creating an effortless

Meg Bodnar Tea Lane Associates

139 Tea Ln, Chilmark, MA 02535
/28
$1,350,000

$49K PRICE DROP
- 2 Beds
- 1 Bath
- 1,996 Sq Ft
29 Scotchmans Ln, Vineyard Haven, MA 02568

Discover the charm of West Tisbury with the perfect blend of country living and village convenience. Ideally located just a short stroll from the heart of town, you'll enjoy easy access to all the West Tisbury Village has to offer. Set on a lovely lot, the home features a spacious southeast-facing deck overlooking a sunny yard. Four detached outbuildings offer exciting possibilities for artists,

Diana Gilmore Island Real Estate

29 Scotchmans Ln, Vineyard Haven, MA 02568
/2
$794,000
- 2 Beds
- 1 Bath
- 624 Sq Ft
60R Carol Ln, Oak Bluffs, MA 02557

Tucked away down a quiet lane just moments from downtown Oak Bluffs, sits this charming home. Nestled on just over an 8,400 sq. ft. lot, the property offers compact single-story living, ideal for those seeking simplicity while being close to everything the island. The bright, open concept features a living area and kitchen with breakfast bar. Ample storage and a stackable washer/dryer complete

Michele Moore Island Real Estate

60R Carol Ln, Oak Bluffs, MA 02557
/29
$1,995,000

Open Tue 10AM - 11:30PM
- 3 Beds
- 2.5 Baths
- 1,439 Sq Ft
33 Vineyard Ave, Oak Bluffs, MA 02557

Welcome to 33 Vineyard Avenue in Oak Bluffs, Martha's Vineyard. This fully gut renovated property 3B/2Ba in total features a 2BR/2BA primary home plus a distinctly separate attached 1BR/1BA ADU suite - offering flexible, move-in ready living or investment potential in a prime in-town location. The main residence in the primary showcases a light-filled interior, wood floors, beamwork, and refined

Allison Cameron Parry Douglas Elliman of MA, LLC

33 Vineyard Ave, Oak Bluffs, MA 02557
/12
$3,400,000

New Construction
- 3 Beds
- 4.5 Baths
- 3,260 Sq Ft
27 Double Ox Rd, Oak Bluffs, MA 02557

Set on a private 1.34-acre parcel along a winding paved road in Oak Bluffs, this exceptional to-be-built luxury residence offers the perfect blend of modern sophistication and island charm. The home features over 3,200 square feet of beautifully crafted living space, including a first-floor primary suite, open-concept great room, gourmet kitchen with pantry, and seamless indoor-outdoor living

Lesley Heidt Sandpiper Realty, Inc.

27 Double Ox Rd, Oak Bluffs, MA 02557
/9
$1,200,000
- Land
- 3.42 Acres
- $350,877 per Acre
23 Onkokemmy Rd Unit 12, West Tisbury, MA 02557

Just beyond the Great White Oak and down scenic Rogers Path, this pastoral West Tisbury parcel offers nearly 3.5 acres of privacy and natural beauty. Moments from the village center yet tucked into a peaceful landscape, the property presents an opportunity to create a custom Vineyard compound. As you traverse your own grove of majestic oak trees, the landscape opens to an idyllic pasture dotted

Katherine Donahue Sandpiper Realty

23 Onkokemmy Rd Unit 12, West Tisbury, MA 02557
/37
$3,750,000
- 4 Beds
- 3 Baths
- 2,204 Sq Ft
9 Weston Ave, Oak Bluffs, MA 02568

This beautifully situated 4-bedroom, 3-bath home sits at the highest point of East Chop, offering sweeping views of Vineyard Sound. The property features a spacious clerestory living room with a fireplace, along with a combined family room and kitchen, also centered around a cozy fireplace. A large, screened porch opens onto an expansive deck, perfect for relaxing or entertaining. The first floor

Gerrett Conover Landvest MV

9 Weston Ave, Oak Bluffs, MA 02568
/40
$1,750,000
- 3 Beds
- 3.5 Baths
- 2,376 Sq Ft
28 Grovedale Rd, Oak Bluffs, MA 02557

GORGEOUS NEWER CONSTRUCTION (2023), contemporary farmhouse style home w/ classic wrap around porch & designed w/ Vineyard charm & modern comfort. And yet still there is opportunity to add value to this open concept home, w/ high ceilings, 3 en-suite BRs, laundry on each level, hardwoods throughout. Well designed, fully poured unfinished basement w/ high ceilings, wide open & w/ a separate

David White OwnerEntry.com

28 Grovedale Rd, Oak Bluffs, MA 02557
/9
$1,200,000
- Land
- 3.42 Acres
- $350,877 per Acre
23 Onkokemmy Rd, West Tisbury, MA 02557

Just beyond the Great White Oak and down scenic Rogers Path, this pastoral West Tisbury parcel offers nearly 3.5 acres of privacy and natural beauty. Moments from the village center yet tucked into a peaceful landscape, the property presents an opportunity to create a custom Vineyard compound. As you traverse your own grove of majestic oak trees, the landscape opens to an idyllic pasture dotted

Katie Donahue & Rachel Serwa Group Sandpiper Realty, Inc.

23 Onkokemmy Rd, West Tisbury, MA 02557
/110
$2,000,000
- 4 Beds
- 6 Baths
- 2,972 Sq Ft
398 Main St, Vineyard Haven, MA 02568

Ideally situated on Main Street in Vineyard Haven, just moments from the Yacht Club and West Chop, this charming four-bedroom, six-bathroom home offers the perfect blend of convenience, comfort, and Island living. Set on a quarter-acre lot, the property features a private and inviting backyard—ideal for entertaining, gardening, or simply enjoying warm summer evenings. Inside, generous living

Peter Cronig Cronigs Real Estate

398 Main St, Vineyard Haven, MA 02568
/34
$1,995,000
- 5 Beds
- 3 Baths
- 3,480 Sq Ft
135 Mayflower Ln, Vineyard Haven, MA 02568

Ideally situated just minutes from the ferry, downtown Vineyard Haven, and West Tisbury, this charming, meticulously maintained property offers exceptional flexibility for year-round living, seasonal escape, or income potential. The main residence features three bedrooms and an inviting open-concept floor plan, seamlessly connecting an updated kitchen, living room, and dining area, perfect for

Kathleen Dawson Donnelly + Co.

135 Mayflower Ln, Vineyard Haven, MA 02568
/26
$3,850,000
- Land
- 1.14 Acres
- $3,377,193 per Acre
10 Pease Point Rd Unit 57, Edgartown, MA 02539

PRIME 1.14 ACRE PROPERTY IN EDGARTOWN This conforming R-20 lot offers an exceptional canvas for your estate planning vision. Positioned at the end of a private drive, on an elevated parcel amid a neighborhood of distinguished new homes, the original three-bedroom, two-bath residence provides a foundation from which to create a truly signature property. Ideally situated just minutes from Edgartown

Emma Bryant Studio Realty

10 Pease Point Rd Unit 57, Edgartown, MA 02539
/31
$15,400,000
- 6 Beds
- 9 Baths
- 6,967 Sq Ft
8 Snail Rd, Chilmark, MA 02535

Horizon House sits atop one of Chilmark's most private and elevated parcels, offering protected and sweeping views of the Atlantic Ocean. Framed by meadow, mature trees, stone walls, and native terrain, the estate holds an extraordinary connection to both land and sea. The 4+ bedroom main house has been thoughtfully reimagined for today's buyer, designed and built by a team of leading architects

Brian Dougherty Corcoran Property Advisors

8 Snail Rd, Chilmark, MA 02535
/38
$3,099,000

$100K PRICE DROP
- 3 Beds
- 3.5 Baths
- 3,082 Sq Ft
53 Stoney Hill Rd, Vineyard Haven, MA 02568

This custom-built Martha’s Vineyard residence blends timeless elegance with contemporary luxury, offering exclusive access to Lambert’s Cove Beach.At its heart is a chef’s kitchen with bespoke cabinetry, honed Carrara marble, Wolf and Sub-Zero appliances, Miele dishwasher, and Hudson Valley lighting. An adjacent custom bar features Dolomite Italian granite, ideal for entertaining.The home boasts

Jennifer B. DaSilva Compass

53 Stoney Hill Rd, Vineyard Haven, MA 02568
/31
$1,790,000
- 3 Beds
- 2.5 Baths
- 2,347 Sq Ft
41 & 0 Cook Rd, Vineyard Haven, MA 02568

Included in the asking price are two separate parcels: a beautifully updated 3-bedroom home and an adjacent 16,000 square foot buildable lot. No subdivision is required. The lot is ready to build on immediately or may be sold separately after closing, offering exceptional flexibility for a family compound, second home, or investment. An easement is being established along the existing driveway to

Jennifer O'hanlon Compass

41 & 0 Cook Rd, Vineyard Haven, MA 02568
/56
$3,695,900
- 3 Beds
- 4.5 Baths
- 3,056 Sq Ft
9 Thaxter Ln, Edgartown, MA 02539

A CONTEMPORARY KATAMA RETREAT, NEWLY REFRESHED AND READY FOR SUMMER. Set in one of Edgartown’s most coveted coastal enclaves, this contemporary retreat captures the effortless rhythm of Katama living: sun-filled interiors, generous gathering spaces, ocean breezes, and a private backyard oasis designed for long summer days by the pool. Moments from South Beach, this tri-level contemporary offers

Wendy Harman

Compass | Point B

9 Thaxter Ln, Edgartown, MA 02539
/26
$949,000
- 3 Beds
- 2 Baths
- 1,328 Sq Ft
96 Dunham Ave, Vineyard Haven, MA 02568

NESTLED ON AN OVERSIZED LOT in a highly convenient Vineyard Haven location, this classic 1972 center-entrance Colonial offers timeless charm and exceptional potential. Inside, an inviting open-concept living space is anchored by a wood-burning fireplace, while soaring vaulted ceilings over the dining area and kitchen create an airy, light-filled atmosphere ideal for gathering with family and

Leslie C. Floyd Portfolio Properties

96 Dunham Ave, Vineyard Haven, MA 02568
/19
$1,150,000

$45K PRICE DROP
- 3 Beds
- 2 Baths
- 1,100 Sq Ft
34 10th St S, Edgartown, MA 02539

Easy Edgartown living awaits in this charming 3-bedroom, 2-bath ranch offering comfort, convenience, and classic Vineyard appeal. Designed for effortless single-level living, the home features a spacious living room, an open kitchen and dining area, and a thoughtful layout that works beautifully for everyday life, entertaining, or relaxed seasonal stays. The private primary suite includes its own

Chrissie Teague Insight Realty Group, Inc.

34 10th St S, Edgartown, MA 02539
/36
$1,349,000

Open Sat 10AM - 12PM $50K PRICE DROP
- 4 Beds
- 2 Baths
- 1,436 Sq Ft
145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575

This coastal contemporary residence is located on a private 1.60-acre lot in West Tisbury, with convenient access to Long Point Wildlife Refuge and access to "Coveted" Lambert's Cove Beach. The home features four bedrooms and two full bathrooms. On the first floor, you'll find two bright bedrooms, a modernized bathroom, and sliders from the living area that lead to a new AZEK deck and enclosed

Marilyn Moses Ocean Park Realty Inc

145 Vineyard Meadow Farms Rd, West Tisbury, MA 02575
/20
$325,000

$5K PRICE DROP
- Land
- 7,405 Sq Ft
- $1,911,765 per Acre
00 Moshup Trail, Aquinnah, MA 02535

Tucked along the south shore of Aquinnah on Martha's Vineyard, this beach lot presents a chance to enjoy true oceanfront ownership. Accessed via Moshup Trail, this lot features a private gated entry with a pea stone parking area. A boardwalk, that winds through natural coastal vegetation, connects to a sandy trail that brings you over the bluff to the expansive shoreline. Secure your own stretch

Sheila Morse Island Real Estate

00 Moshup Trail, Aquinnah, MA 02535
/32
$5,200,000
- 5 Beds
- 3.5 Baths
- 4,044 Sq Ft
49 Gosnolds Way, Chilmark, MA 02535

Set high on the north shore with panoramic views of Vineyard Sound and deeded private beach access, this secluded 9.8-acre estate enjoys a rare setting abutting conservation land and the Menemsha Hills trail network. The meticulously maintained residence features a reverse floor plan designed to maximize natural light, soaring ceilings, and stunning water views. The upper level offers an

Bonnie Pierce Wallace & Co. Sotheby's International Realty

49 Gosnolds Way, Chilmark, MA 02535
/32
$1,150,000

$25K PRICE DROP
- 4 Beds
- 2 Baths
- 2,059 Sq Ft
4 Rock Pond, West Tisbury, MA 02575

4 Rock Pond Road offers a rare opportunity to enjoy the best of community-centered living in one of Martha’s Vineyard’s most unique and thoughtfully designed neighborhoods. Located within the Island Cohousing community in West Tisbury, this 4-bedroom, 2-bath home combines warmth, functionality, sustainability, and connection in a peaceful natural setting.Built by South Mountain Company, the

Trish Lyman Compass | Point B

4 Rock Pond, West Tisbury, MA 02575
/30
$1,850,000
- 4 Beds
- 2.5 Baths
- 2,064 Sq Ft
99 Old Purchase Rd, Edgartown, MA 02539

Enjoying a private setting at the end of a quiet Edgartown cul-de-sac, this post-and-beam home is set on .71 acres with easy access to more than 25 acres of Land Bank conservation land. Conveniently located near Morning Glory Farm, the bike path, downtown Edgartown, and South Beach, the property offers both privacy and accessibility. Filled with natural light, the home features a well-designed

Stephanie Roache Donnelly + Co

99 Old Purchase Rd, Edgartown, MA 02539
/50
$1,800,000
- 4 Beds
- 3 Baths
- 3,158 Sq Ft
188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568

House & Guesthouse near Long Point Beach! The Island's coveted south shore is just minutes from this charming West Tisbury compound, where the connection to nature is seamless. The main house sits high atop the trees and overlooks a park-like, fenced-in backyard perfect for kids and dogs. The yard also encompasses a sweet vegetable garden, a storage shed, and outdoor shower. Inside is open with

Idalyn Macchia Gilstad Wallace & Co. Sotheby's International Realty

188 Vineyard Meadow Farms Rd, West Tisbury, MA 02568
/35
$5,200,000
- 5 Beds
- 3.5 Baths
- 4,044 Sq Ft
49 Gosnold's Way, Chilmark, MA 02535

Set high on the north shore with panoramic waterviews of Vineyard Sound and deeded private beach access, this secluded 9.8-acre property occupies a rare setting bordered by conservation land and the Menemsha Hills trail network.The spacious, meticulously maintained residence features a reverse floor plan that accentuates the natural light, soaring ceilings, and breathtaking views. The upper

Bonnie Pierce Wallace & Co. Sotheby's

49 Gosnold's Way, Chilmark, MA 02535
/42
$5,400,000
- 3 Beds
- 2 Baths
- 2,710 Sq Ft
35 S Bowl Rd, Chilmark, MA 02535

Rare opportunity in the Seven Gates Farm community of Chilmark. Designed by architects Jane and Christian Langmuir, this exceptional three-bedroom home is set on 5.3 acres of beautifully landscaped grounds. Thoughtfully designed to embrace natural light and its surroundings, the residence blends natural materials with contemporary architectural details.The dramatic great room features a striking

Tina Miller Donnelly + Co.

35 S Bowl Rd, Chilmark, MA 02535

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